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Dick Grayson
Earth-Two # Vera Lovely # Marjory Davenport Earth-2 # Helena Wayne / Huntress - It is clear that, after he watched her grow up and she became the superheroine Huntress, Helena and Dick were in love. She was, however, dating District Attorney Harry Sims. When Sims proposed, Helena was conflicted because of her feelings for Dick Before she could give him an answer, Harry suffered an attack by the Joker which left him comatose. This is the last of the story this author knows, and it is also unknown to him if this has any basis in the Earth-Two reality. Earth-One / Post-Crisis / New Earth # Roberta the Girl Wonder (Star Spangled Comics #103) # Edie (Batman #156) # Bette Kane / Bat-Girl - When these two would have adventure together, sexual/romantic tension inevitably played a part, including at least one kiss. # Lori Elton was Dick’s girlfriend in his early college years, around the same time he was gaining a crush on Barbara. # Barbara Gordon / Batgirl - These two also fought crime side-by-side as teenagers, and had a certain romantic chemistry and tension. While relaxing after a tiring fight, Dick took the time to divulge his feelings for Barbara, only to see that she had seemingly fallen asleep. In fact, she was awake, but was unwilling to respond to his confession. # Koriand’r / Starfire When Koriand'r first encountered teh Titans, In an attempt to learn English, she absorbed the language by planting a kiss on Dick. This left him flustered, but meant nothing romantic at the time. (New Teen Titans #2, 1980) During this time, Dick apparently kissed Raven once (likely for innocent reasons) and, due to her own inexperience in the world (and likely other things affecting her mind?) she came to believe they were in love. It was later explained to her that Dick did not love her, and, in truth, she likely did not really love him. Initially denying his feelings for Kori, Robin realized how much he loved Starfire when her life was threatened by Blackfire during an outer-space adventure ( New Teen Titans #23-25, New Teen Titans Annual #1, 1982). In the heat of the battle, Robin’s burgeoning feelings for Starfire became obvious. The two fell in love and became a couple. It was later revealed in a retcon that Barbara had come to Dick’s apartment once in an effort to kindle something between them, only to be greeted by Kori in her underwear, then walking away crying. The couple faced their greatest challenge when Starfire was forced into an arranged marriage to quell a Tamaranean civil uprising. While Starfire saw this as a marriage of state, Dick felt betrayed and left his alien love on Tamaran (New Teen Titans, vol 2, #15-18, 1986). Stafire eventually returned to earth, and reconciled with Dick once he learned she did not take the traditional Tamaranean wedding vows (#39, 1988). The shape-shifter Mirage even kidnapped and impersonated Starfire, causing strain in her relationship with Nightwing. Impulsively, Dick proposed marriage to the tempestuous Tamaranean, desperately hoping to mend their relationship. Dick was off-planet when Barbara was paralyzed. When arrived and heard the news, he came to her apartment, and the two fell into an embrace, sleeping together. Afterwards, he gave her an invitation to his and Kori’s wedding, causing an infuriated Barbara to kick him out. This type of behavior was later attributed to an evil possession on Dick’s part. Dick and Kory's wedding ceremony was interrupted by Raven, now reborn as an evil avatar of her father, Trigon (#99-100, 1993). Starfire was implanted with a demon “seed” by Raven, which caused her to leave Earth and go on a spiritual journey (NTT#114 & Showcase ’94 #11, 1994). Thus, the long-standing relationship of Nightwing and Starfire was at an end, with neither party acquiring much closure. Kory later returned to Earth. Although they have succumbed to old passions more than once, the pair have decided to remain good friends above all else. 5. Bridget Clancy was the superintendent of Dick’s apartment complex when he first moved to Bludhaven. Both seemed to want more, but then Dick began to grow closer with Barbara again, and Bridget moved away. Dick and Babs eventually began dating, and became engaged. But they too eventually broke up. Dick has also been the unrequiting recipient of the teenage Supergirl’s affections after her return in the 2000s, with her planting a kiss on him. He even had Catwoman kiss him at one point, just to make Batman jealous. New 52 # Koriand’r/ Starfire - Dick apparently has a similar history with Kori in the New 52. In an issue of Red Hood, after returning from Tamaran, she says she can no longer remember Dick’s name, or many details about him, as Tamaranians lose their memories when they leave a planet (or some crap like that). It later turns out she was probably largely fibbing about this. # Shawn Tsang / Defacer - This leader of a group of rowdy outlaws also held a position at the community center where Dick Grayson volunteered, and as such, they know each other in both lives, having a sort of Batman-Catwoman relationship. After giving up her criminal ways, and having Nightwing help her and her old gang out of a jam, she confesses that she knows Dick’s true identity, and for a time, the two date. (2016-???) # Barbara Gordon / Batgirl - These two often flirted while fighting crime together. Eventually, Dick made it known he wanted more from their relationship, but she chose insted to date Luke Fox / Batwing. ' I have also heard it said that Dick has recently had a string of bad relationships, the other names mentioned being Raya, and Deborah, and possibly more. He has apparently also been the unrequiting recipient of affections from women named Jessica Cruz and Sophia. I assume most of these to be in the New 52? '''Elseworlds and Alternate Universes' Kingdom Come # Koriand'r / Starfire - In this continuity, they are married with a daughter. Adaptations DC Animated Universe # Barbara Gordon / Batgirl and Dick dated before they realized each other’s alter egos, and at least had an attraction to each other after.. In Batman & Harley Quinn, which is reputed to be apart of the DCAU, Dick has a sexual encounter with Harley Quinn while she has him tied up as her prisoner. Batman & Robin # Barbara Wilson / Batgirl - Dick has an immediate attraction to Alfred's niece, who later becomes his teammate and, apparently, housemate. Teen Titans # Koriand'r / Starfire - Apparently these two have a romantic tension here. DC Animated Movie Universe # Koriand'r / Starfire - They also share at least a tension here.' ' Other Alternate Futures The specifics of these are unknown to me, except that in some he ends up with Kori, and in others, Barbara, and in one, Bette Convergence Future’s End Batman Annual: 40 Years Later Endgame Nightwing: Origins (Marries Bette)